KR20190084317A - Cyclic ketals as perfume precursor compounds - Google Patents

Abstract

FIELD OF THE INVENTION [0002] This invention relates to the field of light-air fresheners used, for example, in detergents and cleaning agents, cosmetic agents and air fresheners. The present invention relates to certain cyclic ketals used as bulb-fragrances. The present invention also relates to detergents and cleaning agents, cosmetic agents and air fresheners containing ketals of this type. The present invention further relates to a method for the production of organ-persistent fragrance on the surface and for combating insects.

Description

Cyclic ketals as perfume precursor compounds

The present invention is directed to the field of air-fresheners as used, for example, in the field of cleaning or cleaning agents, cosmetic agents and air management agents. The present invention relates to certain cyclic ketals that function as bulb-aromatizers. The present invention further relates to cleaning and cleaning agents, cosmetic agents and air management agents containing such a ketal. The present invention further relates to a method for long-lasting smell of a surface.

Washing and rinsing agents and cosmetic agents typically contain a fragrance which imparts a pleasant odor to the agent. The fragrance usually shields the odor of the other ingredients, thus giving the user a pleasant impression of the odor.

In the field of cleaning agents in particular, fragrances are an important component of formulations, since both wet laundry and dry laundry are intended to give a pleasantly pleasant scent. The fundamental problem associated with the use of fragrance is that they want a long-lasting fragrance effect, but they are almost highly volatile compounds. Especially in the case of fragrances that generate a refreshing light note of perfume and which evaporate rapidly, especially due to its relatively high vapor pressure, it is difficult to achieve the desired organ-persistent impression of the fragrance. For example, pro-fragrance molecules, hydrolyzed or photo-labile pro-fragrance molecules, are known in the prior art and represent one option for delayed release of fragrance. The effect of environmental factors results in the partitioning of covalent bonds within the precursor-perfume molecule, thereby releasing the fragrance.

Ketals are known in the prior art as perfumes, and perfume precursors, which are referred to as precursor-perfumes. Ketals as fragrances are disclosed, for example, in International Application WO 2014/183883 Al. The cyclic ketals described in the above document have a direct effect as a fragrance with an amber-greasy flavor. However, there is no mention of a perfume precursor that releases substantial fragrance molecules by hydrolysis of ketals.

International applications WO 97/34986 A1 and WO 97/34989 A1 describe, for example, acetals and ketals as perfume precursors for use in cleaning agents. The ketals described are structurally different from those described herein.

International application WO 01/85713 A1 describes cyclic ketals as an acetophenone perfume precursor.

Finally, German application DE 19718537 A1 also describes depot formulations which are intended for the targeted release of fragrance and which can be obtained by reacting an aromatic aldehyde or ketone with a polyhydroxy compound.

However, when well known bulb-perfume molecules are used, the fragrance strength is low and the perfume effect has only a short duration. Thus, there is also a need for alternative precursor-perfume molecules that effectively emit fragrance and have sufficiently high fragrance strength.

It has surprisingly been found that certain cyclic ketals of formula (I) are suitable for effective release of fragrance under slightly acidic conditions, and thus have higher fragrance strength than known ketals from the prior art.

Thus, in a first aspect, the present invention relates to compounds of formula (I)

here

Ra and Rb together with the C atom to which they are attached form a linear, branched, saturated or unsaturated, branched or cyclic hydrocarbon radical having from 6 to 30, preferably from 6 to 20 carbon atoms and from 0 to 10 heteroatoms selected from N, O, S and Si Or a cyclic, substituted or unsubstituted hydrocarbon functional group or, together with the C atom to which they are attached, form a cyclic hydrocarbon functional group and is derived from a directional ketone of the formula Ra-C (O) -Rb; Each of R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ is independently selected from the group consisting of hydrogen, -OR x, -NR x R y, halogen, a substituent having up to 20, Linear or branched alkyl, alkenyl or alkynyl, up to 20, preferably up to 12 carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, Substituted or unsubstituted, linear or branched heteroalkyl, heteroalkenyl or heteroalkynyl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 20, Substituted or unsubstituted heteroaryl having up to 12 carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, up to 20, preferably up to 12 carbon atoms Lt; RTI ID = 0.0 > cycloalkyl < / RTI & , And heterocycloalkyl or heterocycloalkenyl having up to 20, preferably up to 12, carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N from the group consisting of Or two of R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ in each case are substituted or unsubstituted aryl having up to 20, preferably up to 12 carbon atoms, Substituted or unsubstituted heteroaryl having up to 20, preferably up to 12, carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, up to 20, Substituted or unsubstituted cycloalkyl or cycloalkenyl having up to 12 carbon atoms and up to 20, preferably up to 12 carbon atoms and 1 to 6, preferably 1 < RTI ID = 0.0 > Four to four As may be combined with each other to form click group when selected from substituted or unsubstituted heterocycloalkyl or heteroaryl cycloalkenyl unsubstituted alkenyl having atoms, where _{R 1, R 2, R 3} , R 4, R 5 and R ₆ Is at least one functional group of the formula -ORx or contains a functional group of the above formula as a substituent; Rx and Ry are substituted or unsubstituted, linear or branched alkyl, alkenyl or alkynyl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms And substituted or unsubstituted, linear or branched, heteroalkyl, heteroalkenyl or heteroalkynyl having 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, up to 20, Substituted or unsubstituted aryl having up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms, and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, Cycloalkyl or cycloalkenyl having up to 20, preferably up to 12 carbon atoms, and up to 20, preferably up to 12 carbon atoms and O, S and N U From 1 to 6 selected, and preferably is selected from heterocycloalkyl or heteroaryl, cycloalkenyl having from 1 to 4 heteroatoms; n is 0, 1, 2 or 3;

In another aspect, the invention is directed to a cleaning or cleaning agent comprising at least one compound of formula (I) as described herein.

A further subject of the invention is a cosmetic agent comprising at least one of the compounds of formula (I) as described herein.

Another further object of the present invention is an air management agent comprising at least one of the compounds of formula (I) according to the invention.

Still another object of the present invention is an insect repellent agent containing at least one of the compounds of formula (I) according to the present invention.

Finally, the invention further relates to a method for long-lasting smell of a surface, wherein the compound as described herein is applied to the surface to be smudged and the surface is subsequently exposed to conditions that lead to the release of the smudge ≪ / RTI >

As used herein, "at least one" refers to one or more, for example, 2, 3, 4, 5, 6, 7, 8, 9 or more species. With respect to the constituents of the compounds described herein, this specification does not refer to the absolute amount of the molecule, but rather to the type of constituent. Thus, "at least one compound of formula (I) " means, for example, one or more different compounds of formula (I), i.e. one or more different types of compounds of formula (I). In the stated amounts, the stated amounts refer to the total amount of the correspondingly designated type of component as defined above.

The cyclic ketals according to the invention are compounds of formula (I).

In the above formulas, Ra and Rb together with the C atom to which they are attached have 6 to 30, preferably 6 to 20, carbon atoms and 0 to 10 heteroatoms selected from N, O, S and Si Linear, branched or cyclic, substituted or unsubstituted hydrocarbon functional groups. In various embodiments, Ra, Rb and the C atom to which they are attached are substituted or unsubstituted, linear or branched alkyl, alkenyl or alkynyl having up to 20, preferably up to 12 carbon atoms, up to 20 Substituted or unsubstituted, linear or branched heteroalkyl having 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, preferably up to 12 carbon atoms, heteroalkenyl Or heteroalkynyl, substituted or unsubstituted aryl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms and from 1 to 6 Substituted or unsubstituted heteroaryl having preferably 1 to 4 heteroatoms, cycloalkyl or cycloalkenyl having up to 20, preferably up to 12 carbon atoms, and up to 20, Preferably from a maximum of 12 carbon atoms and O, S, heterocycloalkyl or heterocycloalkyl selected from alkenyl functional groups having 1 to 6 selected from N, preferably of one to four heteroatoms. Finally, Ra and Rb may also be combined to form a cyclic group with the carbon atoms to which they are attached. These cyclic groups are, depending on the specific functional groups, in particular substituted or unsubstituted aryl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms and O, S And substituted or unsubstituted heteroaryl having 1 to 6, preferably 1 to 4, heteroatoms selected from N, substituted or unsubstituted cycloalkyl having up to 20, preferably up to 12 carbon atoms, or Cycloalkenyl, and substituted or unsubstituted heterocycloalkyl having up to 20, preferably up to 12 carbon atoms and 1 to 6, preferably 1 to 4 heteroatoms selected from O, S and N, or Heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group, selected from heterocycloalkenyl. In the selection of the functional groups Ra and Rb, there is a clue that they are selected to be derived from the aromatic ketone of the formula Ra-C (O) -Rb. This directional ketone can be re-released by hydrolysis of the ketal. If the aromatic ketone is, for example, an aliphatic ketone such as undecane-2-one, this means that for compounds of formula (I), Ra is methyl and Rb is n-nonyl or vice versa. If the directional ketone is, for example, acetophenone, then this means that for compounds of formula (I), Ra is methyl and Rb is phenyl, or vice versa. R a and R b together form a functional group of the formula -CH ₂ -CH (CH ₃ ) -CH ₂ -CH ₂ -CH (CH (CH ₃ ) ₂ ) -, if the aromatic ketone is, for example, menthone.

In the compounds of formula (I), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are each independently of the other hydrogen, -OR x, -NR x R y, halogen, A substituted or unsubstituted, linear or branched alkyl, alkenyl or alkynyl having 12 carbon atoms, up to 20, preferably up to 12 carbon atoms and 1 to 6, preferably 1 to 6, selected from O, S and N Substituted or unsubstituted, linear or branched heteroalkyl, heteroalkenyl or heteroalkynyl having from 1 to 4 heteroatoms, substituted or unsubstituted heteroatoms having up to 20, preferably up to 12 carbon atoms, Aryl, substituted or unsubstituted heteroaryl having up to 20, preferably up to 12 carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, up to 20, Preferably up to 12 carbon atoms, Haloalkyl or cycloalkenyl, and heterocycloalkyl or heterocycloalkyl having up to 20, preferably up to 12 carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, ≪ / RTI > alkenyl. However, it is also possible in each case to combine two of R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ together to form a cyclic group with the carbon atom to which they are attached. Wherein the cyclic group may be an aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl or heterocycloalkenyl group having the abovementioned number of carbon atoms and optionally a heteroatom, depending on the specific functional group. In this class of embodiments in which the functional groups are combined to form cyclic groups, each functional group may also be a bond or a heteroatom such as O, S or NRy. In the compounds of formula (I) according to the invention, the moiety of cyclic ketals bearing functional groups R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ is preferably at least 3, Is derived from a polyol or saccharide having at least 4, 5 or 6 hydroxyl groups. Thus, _{R 1, R 2, R 3} , R _4, R ₅ and R ₆ contains at least one of a functional group or a substituent or functional group of the formula of formula -ORx, or _{R 1, R 2, R 3} , It is a clue of the present invention that two of R ₄ , R ₅ and R ₆ together form a functional group of the formula -O-.

Rx and Ry are substituted or unsubstituted, linear or branched alkyl, alkenyl or alkynyl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms And substituted or unsubstituted, linear or branched, heteroalkyl, heteroalkenyl or heteroalkynyl having 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, up to 20, Substituted or unsubstituted aryl having up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms, and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, Cycloalkyl or cycloalkenyl having up to 20, preferably up to 12 carbon atoms, and up to 20, preferably up to 12 carbon atoms and O, S and N U From the selected one to six, preferably it is selected from heterocycloalkyl or heterocycloalkyl-alkenyl having 1 to 4 heteroatoms. However, they are preferably H. In various embodiments where two of R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are combined with each other to form a cyclic group with the carbon atoms to which they are attached, R x is also a group -OR x, There are functional groups of the formula -O- or -NRy- which are excluded from NRxRy and link two carbon atoms.

n is 0, 1, 2 or 3, preferably 0 or 1.

In a preferred embodiment, compounds wherein n is 0 and Ra and Rb are both phenyl and / or n is 0 and Ra or Rb is methyl and the other functional group not selected from Ra or Rb is pentyl is not claimed.

The ketal is preferably formed by a neighboring site of the polyol or saccharide, or a gamma-permanent hydroxyl group, which forms the body of the ketal with the keto group of the aromatic ketone. This produces a 5-membered or 6-membered ring, i.e. a 1,3-dioxolane or 1,3-dioxane ring in which the functional group of the aromatic ketone is attached to the C2 atom.

As used herein, "alkyl" refers to saturated aliphatic hydrocarbons, including straight and branched chain groups. The alkyl group preferably has 1 to 10 carbon atoms (for example, when the numerical range "1 to 10" is specified herein, it means that the group (in this case the alkyl group) Up to 10 carbon atoms, one carbon atom, two carbon atoms, three carbon atoms, etc.). In particular, alkyl is an intermediate alkyl having 1 to 6 carbon atoms or a lower alkyl having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, butyl, iso-butyl, And so on.

"Alkenyl" means an alkyl group as defined herein, consisting of at least two carbon atoms and at least one carbon-carbon double bond, such as ethenyl, propenyl, butenyl or pentenyl, Such as 1-propenyl or 2-propenyl, 1-butenyl, 2-butenyl or 3-butenyl, and the like.

"Alkynyl" means an alkyl group as defined herein, such as ethynyl (acetylene), propynyl, butynyl or pentynyl, consisting of at least two carbon atoms and at least one carbon- Quot; refers to its structural isomer as described above.

As used herein, "heteroalkyl "," heteroalkenyl ", and "heteroalkynyl" are each as defined above wherein at least one carbon atom is replaced by a heteroatom selected from O, S, Refers to the same alkyl, alkenyl and alkynyl groups, such as ethoxyethyl, ethoxyethenyl, isopentoxypropyl and alkoxy functional groups of the formula -O-alkyl, such as methoxy, ethoxy, propoxy, do. In this kind of functional group, it is preferable that no two heteroatoms are directly bonded to each other, that is, no structural unit of the formula -O-O- or any similar structure is contained at all.

The term "cycloalkyl" group refers to a monocyclic or polycyclic (multicyclic ring having a shared carbon atom) group, especially consisting of 3 to 8 carbon atoms, wherein the ring is a group that does not have any double bonds, Such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. Examples of cycloalkyl groups are cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane and cycloheptane. Thus, "cycloalkenyl" refers to the corresponding cyclic group that has at least one double bond, but does not have a fully conjugated pi electron system, i.e., is not aromatic. Examples of such functional groups are cyclobutenyl, cyclopentenyl, cyclohexenyl, and the like. Cycloalkenyl groups include, but are not limited to, cyclopentene, cyclohexene, cyclohexadiene, and cycloheptatriene.

"Aryl" refers to a monocyclic or polycyclic (i. E., A ring having a pair of shared neighboring carbon atom pairs) groups, especially of 6 to 14 carbon ring atoms, having a fully conjugated pi electron system. Examples of aryl groups are phenyl, naphthalenyl, and anthracenyl.

The "heteroaryl" group refers to a monocyclic or polycyclic (i. E., A group of adjacent ring atoms ") that is composed of 5 to 10 ring atoms in particular, wherein 1, 2, 3 or 4 ring atoms are nitrogen, Quot; refers to an aromatic ring. Examples of heteroaryl groups include pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 1,2,3-triazolyl, , 4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 4-thiazinyl, 1,2,3-triazinyl, benzofuryl, isobenzofuryl, benzothienyl, benzotriazolyl, isobenzothienyl, indolyl, isoindolyl, 3H-indolyl, benzimidazolyl , Benzothiazolyl, benzoxazolyl, quinolizinyl, quinazolinyl, phthalazinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, quinolyl, isoquinolyl, tetrazolyl, 5,6,7,8 -Tetrahydroquinolyl, 5,6,7,8-tetrahydroisoquinolyl, purinyl, pteridinyl, pyridinyl, pyrimidinyl, carbazolyl, xanthanyl or benzoquinolyl.

"Heterocycloalkyl" group refers to a monocyclic or fused ring consisting of 5 to 10 ring atoms, containing 1, 2 or 3 heteroatoms selected from N, O and S and the remainder of the ring atoms being carbon do. The "heterocycloalkenyl" group additionally contains one or more double bonds. However, the ring does not have a completely conjugated pi electrograph. Examples of the heteroalicyclic group include pyrrolidine, piperidine, piperazine, morpholine, imidazolidine, tetrahydropyridazine, tetrahydrofuran, thiomorpholine, tetrahydropyridine and the like.

"Substituted ", as used herein with respect to the substituents and functional groups according to the present invention, means that at least one H atom in the group is replaced by another functional group, and these functional groups are especially those containing at least one heteroatom ≪ / RTI > In various embodiments, the substituent is = O, = S, -OH, -SH, -NH 2 -NO 2, -CN, -F, -Cl, -Br, C 1-10 alkyl, C _2-10 alkenyl , C _2-10 alkynyl, C _3-8 cycloalkyl, C _6-14 aryl, a 5-10-membered heteroaryl ring in which one to four ring atoms are independently nitrogen, oxygen or sulfur, and one to three ring atoms Membered heterocyclic ring which is independently nitrogen, oxygen or sulfur.

In various embodiments of the invention, the compounds according to the invention are those of formula (II)

In the above formula, Ra, Rb, R ₁ , R ₂ , R ₄ , R ₅ , R ₆ and n are defined as above. Further, Ra ', Rb', R ₁ ', R ₂ ', R ₄ ', R ₅ ' and R ₆ 'are the same as R a, R b, R ₁ , R ₂ , R ₄ , R ₅ and R ₆ But are independently selected. Rc and Rd are independently selected from the group consisting of hydrogen, -ORx, -NRxRy, halogen, substituted or unsubstituted, linear or branched alkyl, alkenyl, or alkynyl having up to 20, preferably up to 12 carbon atoms, Substituted or unsubstituted, linear or branched, heteroalkyl having 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, Substituted or unsubstituted aryl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms and 1 to 6 selected from O, S and N, Preferably a substituted or unsubstituted heteroaryl having 1 to 4 heteroatoms, cycloalkyl or cycloalkenyl having up to 20, preferably up to 12 carbon atoms, and up to 20, preferably up to 20, Heterocycloalkyl or heterocycloalkenyl having 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, wherein Rx and Ry are defined as above . However, Rc and Rd of the one is the R _1, R _2, to form a cyclic together with the carbon atoms to which they are attached they _{R 3, R 4, R 5} , R 6, R 1 ', R 2', R 3 ', R ₄ ', R ₅ 'and R ₆ '. Wherein the cyclic group may be an aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl or heterocycloalkenyl group, depending on the specific functional group. In this class of embodiments in which the functional groups are combined to form cyclic groups, each functional group may also be a bond or a heteroatom such as O, S or NRy. Rc or Rd is a group of the formula -ORx where Rx = H or a group of the functional groups R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₁ ', R ₂ ', R ₃ ', R ₄ ', R _5' and R ₆ with one of the dogs, it is preferable to form a group of the formula -O-. m is 0 or an integer from 1 to 10, preferably 0, 1, 2 or 3, particularly preferably 1 or 2, most preferably 2.

In various embodiments of compounds of formula (II), the sum of n and m in all cases is 1, 2, 3 or 4, preferably 2. This means, for example, that in both cases n is 0 and m is 2, or that in one case n is 1 and n in one case is 0 and m is 1.

In the compounds of formula (II) according to the present invention, the functional group _{R 1, R 2, R 3} , R 4, R 5, R 6, R 1 ', R 2', R 3 ', R 4', R 5 ' And R ₆ 'are preferably derived from polyols or saccharides such as mannitol or L-sorbose having at least 3, preferably at least 4, 5 or 6 hydroxyl groups.

Generally, the polyol or saccharide forming the ketal backbone is preferably selected from the group consisting of glycerol, mannitol, isomaltol, lactitol, sorbitol (or glucitol) and xylitol, traitol, erythritol, arabitol, But are not limited to, lactose, threose, ribose, arabinose, xylose, ricosource, aloose, altrose, glucose, mannose, gulose, idose, galactose, talose, erythrulose, ribulose, xylulose, ≪ / RTI > fructose, fructose, sorbose and tagatose. Simple sugars can be used in D or L form, but typically in its D form.

In various preferred embodiments, R ₁ , R ₂ and R ₄ of the compounds of formula (I) are hydrogen. R ₃ is preferably a substituted alkyl or heteroalkyl functional group having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms, and optionally 1 or more oxygen atoms. In such embodiments, the alkyl functionality is preferably substituted with at least one hydroxyl group. In particular, in this kind of embodiment, R ₃ can be, for example, a functional group having a second cyclic ketal group of the formula - (CRcRd) _m - (cyclic ketal). In this class of embodiments, the result is a compound of formula (II). When n is 1 or more, R < ₅ > is preferably H and R < ₆ > is preferably not hydrogen, but rather preferably -OH.

In compounds of formula (II), R ₁ , R ₂ , R ₄ , R ₁ ', R ₂ ' and R ₄ 'are hydrogen in various embodiments. In all cases, n is preferably 0 or 1, particularly preferably 0. [ R ₅ or R ₅ 'is preferably H and R ₆ or R ₆ ' is preferably not hydrogen but rather preferably -OH, or R ₄ or R _4, and with (R ₆ is R ₄ 'and R ₆ together or' together with R _4), to form a group of the formula -O-. In this class of embodiments, m is preferably 1 or 2. Where Rc is preferably H and Rd is preferably-OH. In this kind of embodiment, the sum of n and m in all cases is preferably 2.

Particularly preferred compounds of formula (II) are those of formula (III) and (IV)

In the above formulas, Ra, Rb, Ra 'and Rb' are as defined above, and in particular are functional groups derived from aromatic ketones of the formula Ra-C (O) -Rb or Ra'-C (O) -Rb '. Derived functional group "means a functional group derived from an aromatic ketone in that the carbon atom at the C2 position of the cyclic ketal carries an oxygen atom in the aromatic ketone, that is, a carbon atom that forms a keto group. Rb and Ra '/ Rb'. When the fragrance is released, for example by enzymatic or chemical hydrolysis, the ketal is cleaved so that the aromatic ketone and the corresponding polyol are produced as cleavage products.

The compounds of formulas (I) - (IV) according to the invention are suitable as prodrugs for all directional ketones known in the prior art and are suitable for this purpose. As used herein, "aromatic ketone" refers to a natural or synthetic origin fragrance containing at least one keto group.

In various embodiments, the aromatic ketone bound in a cyclic ketal structure according to Formulas (I) - (IV) and capable of being released by hydrolysis is a bichromate; Isozyme; Methyl beta-naphthyl ketone; Musk indanone; Tonal Lead / Musk Plus; Alpha-Damascone, Beta-Damascone, Delta-Damascone, Gamma-Damascone, Damaceonone, Damascene Rose, Methyl dihydrozammonate (Hedione), Menton, Carbon, Camphor, Beta-ionone, gamma-methylionone, pramamone, dihydrozaspone, cis-jasmon, iso E super (1- (1,2,3,4,5,6,7,8- Octahydro-2,3,8,8-tetramethyl-2-naphthyl) ethan-1-one), methyl cedryl ketone, methyl cedriron, acetophenone, methylacetophenone, para-methoxyacetophenone , Methyl beta- naphthyl ketone, benzyl acetone, benzophenone, para-hydroxyphenylbutanone, celery ketone or ribscon, 6-isopropyldecahydro-2-naphthone, dimethyloctenone, (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone, methylheptenone, 2- (2- (4-methyl-3-cyclohexen- , 1- (p-menthene-6 (2) yl) -1-propanone, 4- (4-hydroxy- Butanone, 2-acetyl-3,3-dimethylnorbornane, 6,7-dihydro-1,1,2,3,3-pentamethyl-4 (5H) (5-methyl-5-phenyl-3-hexanone), dulcinyl, kathion, gelson, hexalone, isocyclemone E, methylcyclotetrone, methyl lavender ketone, oribone, para-tert-butylcyclohexanone , Bredon, dulphon, mucone, neobutenone, flicatonone, bellowton, 2,4,4,7-tetramethyl-oct-6-en-3-one and tetramerane.

These are particularly preferably Bucoxime; Isozyme; Methyl beta-naphthyl ketone; Musk indanone; Tonal Lead / Musk Plus; Alpha-Damascone, Beta-Damascone, Delta-Damascone, Gamma-Damascone, Damaceonone, Damascene Rose, Methyl dihydrozammonate (Hedione), Menton, Carbon, Camphor, Beta-ionone, gamma-methylionone, pramamone, dihydrozaspone, cis-jasmon, iso E super (1- (1,2,3,4,5,6,7,8- Octahydro-2,3,8,8-tetramethyl-2-naphthyl) ethan-1-one), methyl cedryl ketone, methyl cedriron, acetophenone, methylacetophenone, para-methoxyacetophenone , Methyl beta-naphthyl ketone, benzyl acetone, para-hydroxyphenylbutanone, celery ketone or ribscon, 6-isopropyldecahydro-2-naphthone, dimethyloctenone, Methyl-3-cyclohexen-1-yl) propyl) cyclopentanone, 1- (2- (p-menthene-6 (2) yl) -1-propanone, 4- (4-hydroxy-3-methoxyphenyl) 2-acetyl-3,3-dimethylnorbornane, 6,7-dihydro-1,1,2,3,3-pentamethyl-4 (5H) indanone, 4- Butyl-cyclohexanone, verdone, dulphon, p-toluenesulfonic acid, p-toluenesulfonic acid, p-toluenesulfonic acid, Moscone, neobutenone, flicatonone, bellowton, 2,4,4,7-tetramethyl-oct-6-en-3-one and tetramerane.

In a preferred embodiment, diphenylmethanone and pinacolone are not claimed.

In general, the following are also suitable directional ketones and the present invention is not limited thereto:

4-methoxyphenyl-ethanone; 1- [6- (1,1-Dimethylethyl) -2,3-dihydro-1,1-dimethyl-1H-inden-4-yl] ethanone; 1- (5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl) ethanone; 2- (1-methylethyl) -indanone; 4-tert-butyl-3,5-dinitro-2,6-dimethyl-acetophenone; 1,6,7,8-tetrahydro-1,4,6,6,8,8-hexamethyl-as-indacene-3 (2H) -one; 1- (2-Daphthalenyl) ethanone; 1- (2,3-dihydro-1,1,2,3,3,6-hexamethyl-1H-inden-5-yl) ethanone; 1- [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1H-inden-5-yl] ethanone; 3-methyl-1- (4-methylphenyl) -4-hexen-1-one; 5-acetyl-1,1,2,3,3-pentamethylindane; 1-phenylpropanone; Acetophenone; 2,4-dimethylphenyl-ethanone; 1- [4- (1,1-dimethylethyl) -2,6-dimethylphenyl] ethanone; 1- (hexahydrodimethyl-1H-benzindenyl) ethanone; 1- (5,6,7,8-tetrahydro-2-naphthalenyl) ethanone; 1-phenyl-4-penten-1-one; 1- (5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl) ethanone; 1- (3-ethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl) ethanone; 2,5-dimethyl-oct-2-en-6-one; 4- (2,6,6-trimethylcyclohex-1-en-1-yl) -butan-2-one; 4- (2,6,6-trimethylcyclohex-2-en-1-yl) -butan-2-one; 2-methyl-5- (1-methylethenyl) -cyclohex-2-en-1-one; 1- (4-hydroxyphenyl) -butan-3-one; 4-Benzo-1, 3-dioxo-5-yl-but-2-one; 2-heptyl-cyclopentanon-nonan-2-one; Oct-2-one; 2,2,6,10-tetramethyltricyclo- [5.4.0.0 (6,10)] undecan-4-one; Heptan-2-one; Undecan-2-one; Decan-2-one; Benzyl acetone; Butan-2-one; 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one; 6-methyl-hept-5-en-2-one; 2- (butan-2-yl) -cyclohexanone; 2-hexyl-cyclopent-2-en-1-one; 2- (1-methylethyl) -5-methyl-cyclohexanone; 2- (2-methylethyl) -5-methyl-cyclohexanone; 3-methyl-cyclopentadecanone; 4- (1,1-dimethylpropyl) -cyclohexanone; 6,10-dimethyl-undeca-5,9-dien-2-one; 3-oxo-2-pentyl-cyclopentane-acetic acid-methyl ester; 1- (1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl) ethanone; 3-methyl-5-propyl-cyclohex-2-en-1-one; 1- (2-cyclohexene) -2,4,4-trimethyl-but-2-enone; Carbon; 2-hexyl-cyclo-pent-2-en-1-one; 2-pentyl-cyclopent-2-en-1-one; 3-methyl-2-pentyl-cyclopent-2-en-1-one; 2-hexylidene-cyclopentanone; 3,5-diethyl-5,6-dimethyl-2-cyclohexenone; 4,4a, 5,6,7,8-hexahydro-6-isopropenyl-4,4a-dimethyl-2 (3H) -naphthalenone; 3-methyl-6-propylidene cyclohexanone; 4- (1-methylethyl) -cyclohex-2-en-1-one; (E) -oct-3-en-2-one; 1- (2,3,4,7,8,8A-hexahydro-3,6,8,8-tetramethyl-1H-3a, 7-methanoazulen-5-yl) -ethanone; 2-hydroxy-3,5-dimethyl-cyclopent-2-en-1-one; 1- (3,3-dimethyl-1-cyclohexen-1-yl) ethanone; 1- (2,4,6-trimethylcyclohex-3-en-1-yl) -but-1-en-3-one; Acetylisothiophenol; 2- (3-methylbut-2-en-1-yl) -3-methyl-cyclopent-2-en-1-one; 3-methyl-5- (2,2,3-trimethylcyclopent-3-en-1-yl) pent-3-en-2-one; 5-butylidene-2,2,4-trimethylcyclopentanone; 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one; 3-methyl-5-propyl-cyclohex-2-en-1-one; 4,4a, 5,6,7,8-hexahydro-6-isopropyl-2 (3H) -naphthalinone; 3,5,5-trimethyl-cyclohex-2-ene-1,4-dione; (E) -5-methyl-2-hepten-4-one; Acetyl diisoamylen; Des-3-en-2-one; 2-ethyl-3,6,6-trimethylcyclohex-2-enyl-but-2-en-1-one; 1- (5,5-dimethyl-1 (6) -cyclohexen-1-yl) -4-penten-1-one; 1- (2,6,6-trimethyl-1-cyclohexen-1-yl) but-2-en-1-one; 1- (2,6,6-trimethyl-2-cyclohexen-1-yl) but-2-en-1-one; 1- (2,6,6-trimethyl-3-cyclohexen-1-yl) but-2-en-1-one; 2,4,4,5,5-Pentamethyl-1-cyclopenten-l-yl-ethanone.

Thus, in various embodiments of the present invention, the compounds of formulas (I) through (IV) correspond to the functional groups of the above-mentioned aromatic ketone in which Ra / Rb and / or Ra '/ Rb' are located on either side of the keto group ≪ / RTI > For example, when undecan-2-one is used as the aromatic ketone, in the compounds of formulas (III) and (IV), Ra and Ra 'are methyl and Rb and Rb' are n-nonyl. For example, when used as a perfume is menthone, each Ra and Rb, and Ra 'and Rb' is a functional group with a _{-CH 2 -CH (CH 3) -CH} 2 -CH 2 -CH (CH (CH 3) 2) -. The above-mentioned specific compounds are embodiments of the present invention.

The compounds according to the present invention can be stably incorporated into typical washing or cleaning agent matrices, cosmetics and conventional perfume compositions. These provide delayed release of the stored directional ketone. A preferred fragrance is, for example, damascone. These fragrances impart a particularly long-lasting refreshing impression to typical washing or cleaning agents and cosmetics. In particular, dry, washed textiles benefit from the excellent fragrance effect of long-term freshness. The stored perfume is released slowly by hydrolysis of the compound, which can be accomplished using enzymes or by acidic or basic media.

A further object of the present invention is a cleaning or cleaning agent, preferably a cleaning agent, a softening agent or an auxiliary cleaning agent, containing at least one compound of formula (I), said compound preferably being in each case an agent Is advantageously contained in an amount of 0.0001 to 5 wt.%, Advantageously 0.001 to 4 wt.%, More advantageously 0.005 to 3 wt.%, Especially 0.01 to 2 wt.%, Based on the total weight of the composition. Suitable rinsing agents are, for example, rinsing agents for hard surfaces, in particular dishwasher detergents. The cleaning agent may also be, for example, household cleaners, multipurpose cleaners, window cleaners, floor cleaners, and the like. In various embodiments, the cleaning agent may be a product for cleaning the toilet and urinal, in particular a flush cleaner for hanging on the toilet.

According to a preferred embodiment of the invention, the cleaning or cleaning agent according to the invention contains at least one surfactant selected from anionic, cationic, nonionic, zwitterionic and amphoteric surfactants or mixtures thereof.

According to a further preferred embodiment of the invention, the agent according to the invention is present in solid or liquid form.

A further object of the present invention is a cosmetic agent containing at least one compound according to formula (I), said agent preferably being present in an amount of from 0.0001 to 50 wt.%, Based on the total agent in each case. %, Advantageously 0.001 to 5 wt.%, More advantageously 0.005 to 3 wt.%, Especially 0.01 to 2 wt.%.

A further object of the present invention is an air control agent (e.g. air freshener, room deodorant, room spray, etc.) containing at least one compound according to formula (I), wherein the compound of formula (I) , In each case from 0.0001 to 50 wt.%, Preferably from 0.001 to 5 wt.%, More preferably from 0.01 to 3 wt.%, Particularly preferably from 0.1 to 2 wt.%, Based on the total weight of the agonist %. ≪ / RTI >

A further object of the present invention is an insect repellent (for example insect spray, fragrant room spray, mosquito net, insect trap, etc.) containing at least one compound according to formula (I) Is preferably present in an amount of from 0.0001 to 50 wt.%, Preferably from 0.001 to 5 wt.%, More preferably from 0.01 to 3 wt.%, Based on the total weight of the agent in each case, 0.1 to 2 wt.%.

According to a further preferred embodiment of the invention, an additional fragrance is contained in the agent according to the invention (i. E. A cleaning or cleaning agent, a cosmetic agent, an air management agent or an insect repellent) , Preferably more volatile fragrances, high boiling fragrances, solid fragrances and / or semi-solid fragrances.

Examples of semi-solid flavors that can be advantageously used within the scope of the present invention include essential oils such as angelica root oil, anise oil, arnica flower oil, basil oil, bay oil, bergamot oil, chumaca flower oil, white fir oil, Ginger oil, guar gum oil, coriander oil, helix oil, hoary oil, ginger oil, iris oil, corn oil, eucalyptus oil, fennel oil, spruce seed oil, galbanum oil, geranium oil, , Cayenne oil, corn oil, chamomile oil, camphor oil, cananaf oil, cardamom oil, cassia oil, pine oil, coffea bar balm oil, coriander oil, spearmint oil, caraway oil, cumin oil, lavender oil , Lemon grass oil, lime oil, mandarin oil, melissa oil, musk seed oil, mir oil, clove oil, Peppermint Oil, Peppermint Oil, Peppermint Oil, Peppermint Oil, Allspice Oil, Pine Oil, Rose Oil, Rosemary Oil, Peppermint Oil, Peppermint Oil, Peppermint Oil, Peppermint Oil, Jelly berry oil, warmwood oil, wintergreen oil, ylang-ylang oil, hyssop oil, sunflower oil, sunflower oil, coconut oil, sandalwood oil, celery oil, spike lavender oil, star anise oil, Cinnamon oil, cinnamon leaf oil, citronella oil, lemon oil and cypress oil.

However, high boiling point and solid flavorings of natural or synthetic origin may also be used as semi-solid flavorings or fragrance mixtures, i.e., perfumes, within the scope of the present invention. These compounds include the following compounds and mixtures thereof: amberlitolide, alpha-amylcinnamaldehyde, anethole, anisaldehyde, anisalcohol, anisole, anthranilic acid methyl ester, acetophenone, benzyl acetone, benzaldehyde, Benzoic acid ethyl ester, benzophenone, benzyl alcohol, benzyl acetate, benzyl benzoate, benzyl formate, benzyl valeritanate, borneol, bornyl acetate, alpha-bromostyrene, n-decyl aldehyde, n-dodecyl aldehyde, Heptinecarboxylic acid methyl ester, heptaldehyde, hydroquinone dimethyl ether, hydroxycinnamaldehyde, hydroxycinnamic aldehyde, hydroxycinnamic aldehyde, hydroxycinnamic acid, Hydroxycinnamoyl alcohol, indole, theory, isougenol, isougenol methyl ether, isosaprol, P-cresol methyl ether, coumarin, p-methoxyacetophenone, methyl n-amyl ketone, methyl anthranilic acid methyl ester, p-methylacetophenone, methyl carbycol, p N-nonyl ketone, methyl n-nonyl ketone, mucone, beta- naphthol ethyl ether, beta- naphthol methyl ether, nerol, nitrobenzene, n-nonyl aldehyde, Butyric acid, salicylic acid methyl ester, salicylic acid methyl ester, salicylic acid methyl ester, salicylic acid methyl ester, salicylic acid methyl ester, salicylic acid methyl ester, salicylic acid methyl ester, salicylic acid methyl ester, Hexyl ester, salicylic acid cyclohexyl ester, santrol, scatol, terpineol, thymene, thymol, gamma-undecalactone, vanillin, veratraldehyde, cinnamaldehyde, cinnamyl alcohol, cinnamic acid, Esters and cinnamic acid benzyl ester. More volatile fragrances particularly include low boiling fragrances of natural or synthetic origin, which may be used alone or as a mixture. Examples of more volatile fragrances are alkyl isothiocyanates (alkyl mustard oil), butanedione, limonene, linaroyl, linacetate and propionate, menthol, mentone, methyl- Phenylacetaldehyde, terpinyl acetate, citral and citronellal.

According to a further preferred embodiment, the agents according to the invention (i.e. washing or cleaning agents, cosmetic agents, air-management agents or insect repellents) comprise at least one, And / or a cosmetic ingredient, which are advantageously selected from the group consisting of anionic surfactants, cationic surfactants, amphoteric surfactants, non-ionic surfactants, acidifying agents, alkalizing agents, anti-wrinkle agents Antioxidants, antiperspirants, antistatic agents, builders, bleaches, bleach activators, bleach stabilizers, bleaching catalysts, ironing aids, nasal builders, fragrances, anti-shrink agents, electrolytes, enzymes, color protectants, colorants , Dyes, antifouling agents, fluorescent agents, fungicides, bactericides, odor-complexing agents, aztans, chelating agents, rinse aids, complexing agents, preservatives, Water-repellent and water-repellent agents, water-miscible organic solvents, optical brighteners, perfumes, perfume carriers, polishes, pH regulators, water repellents and impregnation agents, polymers, swelling and slip agents, Ingredients, UV blocking agents, viscosity modifiers, thickeners, discoloration inhibitors, graying inhibitors, vitamins and / or softeners. In the sense of the present invention, unless otherwise indicated, the amount specified in wt.% Is based on the total weight of the agent according to the invention.

The amount of the individual components in the agent according to the invention (i. E., The cleaning or cleaning agent, the cosmetic agent or the air-management agent) will in each case depend on the intended purpose of the agent in question, , Or they can be obtained from the relevant technical literature. Depending on the intended purpose of the agents according to the invention, for example, the surfactant content is chosen to be more or less. Typically, the surfactant content of the cleaning agent may be, for example, 10 to 50 wt.%, Preferably 12.5 to 30 wt.%, Especially 15 to 25 wt.%, While for example, The rinsing agent for cleaning may contain, for example, from 0.1 to 10 wt.%, Preferably from 0.5 to 7.5 wt.%, Especially from 1 to 5 wt.%, Of a surfactant.

The agents according to the invention (i. E., Cleaning or cleaning agents, cosmetic agents or air-conditioning agents) contain surfactants, preferably anionic surfactants, nonionic surfactants and mixtures thereof, as well as cationic surfactants . Suitable non-ionic surfactants are, in particular, ethoxylated and / or alkylated alkyl glycosides and / or linear or branched alcohols having from 12 to 18 carbon atoms in each alkyl moiety and from 3 to 20, preferably from 4 to 10, / RTI > and / or propoxylated products. With respect to the alkyl moiety, the corresponding ethoxylation of alkylphenols with 5 to 12 carbon atoms in the alkyl functional groups and / or with the N-alkylamines, neighboring diols, fatty acid esters and fatty acid amides corresponding to the specified long chain alcohol derivatives and / Propoxylation products are also available.

Suitable anionic surfactants are in particular soaps and those containing sulphates or sulphonate groups, preferably as alkali cations, as the cation. The soap that can be used is preferably an alkali salt of a saturated or unsaturated fatty acid having 12 to 18 carbon atoms. This type of fatty acid can also be used in a completely non-neutralized form. Sulfate-type surfactants that may be used include salts of sulfuric acid semiesters of fatty alcohols having from 12 to 18 carbon atoms and sulfated products of the mentioned nonionic surfactants with low ethoxylation degree. Sulfonate-type surfactants that can be used include linear alkylbenzene sulfonates having 9 to 14 carbon atoms in the alkyl portion, alkane sulfonates having 12 to 18 carbon atoms, and the corresponding monoolefins resulting from the reaction of sulfur trioxide with sulfur trioxide Olefin sulfonates having 12 to 18 carbon atoms, and alpha-sulfo fatty acid esters resulting from the sulfonation of fatty acid methyl or ethyl esters.

The cationic surfactants are preferably the formula ^{(R I) (R II)} (R III) (R IV) N + X - is selected from quaternary ammonium compounds (QAC), and / or ester quart according to, in which R ^I To R ^IV represent the same or different C _1-22 alkyl, C _7-28 arylalkyl or heterocyclic functional groups wherein two functional groups, or even three functional groups in the case of aromatic bonds such as in pyridine, Together with the nitrogen atom form a heterocycle, for example a pyridinium or imidazolinium compound, and X ^- represents a halide ion, a sulfate ion, a hydroxide ion or a similar anion. QAC can be prepared by reacting a tertiary amine with an alkylating agent, such as methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, as well as ethylene oxide. The alkylation of tertiary amines having one long alkyl functional group and two methyl groups is particularly simple; Quaternization of tertiary amines having two long functional groups and one methyl group can also be carried out using methyl chloride under mild conditions. Amines having three long alkyl functionalities or hydroxy-substituted alkyl functionalities are less reactive and quaternized, for example, using dimethyl sulfate. Examples of suitable QACs include benzalkonium chloride (N-alkyl-N, N-dimethylbenzylammonium chloride), benzalkonium B (m, p-dichlorobenzyldimethyl- _C12 alkylammonium chloride), benzoxonium chloride (N, N-dimethyl-N- [2- (2-hydroxyethyl) ammonium chloride), Rumunium bromide (N-hexadecyl-N, N-trimethylammonium bromide), Benzethonium chloride [2- [p- (1,1,3,3-tetramethylbutyl) phenoxy] ethoxy] ethyl] benzylammonium chloride), dialkyldimethylammonium chloride such as di-n-decyldimethylammonium chloride, Ammonium bromide, dioctyldimethylammonium chloride, 1-cetylpyridinium chloride, and thiazoline iodide, and mixtures thereof. The preferred QAC is C ₈ -C ₂₂ is benzalkonium chloride, in particular C ₁₂ -C ₁₄ alkyl dimethyl benzyl ammonium chloride having an alkyl functional group.

Preferred ester quats are methyl-N- (2-hydroxyethyl) -N, N-di (tert-butylethyl) Trisulfate or methyl-N, N-bis (acyl-oxyethyl) -N- (2-hydroxyethyl) ammonium methosulfate. Commercially available examples include methylhydroxyalkyl dialkyloxyalkylammonium methosulfate, commercially available under the trademark Stepantex® by Stepan, BASF SE, known under the trade name Dehyquart, Lt; / RTI > or from the manufacturer Evonik, known under the name Rewoquat.

The surfactant is preferably present in an amount of from 5 wt.% To 50 wt.%, Especially from 8 wt.% To 30 wt.%, Of the agent according to the invention (i. E., A cleaning or cleaning agent, a cosmetic agent or an air- . Preferably at least partially containing a cationic surfactant, preferably up to 30 wt.%, In particular from 5 wt.% To 15 wt.%, Of a surfactant is used, especially in the post-wash treatment agent.

The agents according to the invention, in particular the cleaning or cleaning agents, preferably contain at least one water-soluble and / or water-insoluble, organic and / or inorganic builder. Water-soluble organic builders include polycarboxylic acids, especially citric and saccharic acids, monomeric and polymeric aminopolycarboxylic acids, especially methyl glycine diacetic acid, nitrilotriacetic acid, ethylenediamine tetraacetic acid and polyaspartic acid, polyphosphonic acid, In particular, aminotris (methylenephosphonic acid), ethylenediaminetetrakis (methylenephosphonic acid) and 1-hydroxyethane-1,1-diphosphonic acid, polymeric hydroxy compounds such as dextrin, and polymeric (poly) , Polymeric acrylic acid, methacrylic acid, maleic acid, and mixed polymers thereof, which may also contain a small proportion of polymeric materials, without carboxylic acid functionality, in the polymer. Suitable but less preferred classes of such compounds are copolymers of acrylic acid or methacrylic acid with vinyl ethers such as vinyl methyl ether, vinyl esters, ethylene, propylene and styrene, wherein the ratio of acid is at least 50 wt.%. The organic builder may be used in the form of an aqueous solution, preferably in the form of an aqueous solution of 30 to 50 wt.%, In particular for the preparation of liquid agents. All the indicated acids are generally used in the form of their water-soluble salts, especially their alkali salts.

The organic builder, if desired, may be present in an amount of up to 40 wt.%, Especially up to 25 wt.%, Preferably 1 wt.% To 8 wt.%. An amount close to the stated upper limit value is preferably used in the paste-form or liquid according to the invention, in particular in water-containing agents. The post-laundry processing agents according to the invention, such as softening agents, may optionally also contain no organic builders.

In particular, alkali silicates and polyphosphates, preferably sodium triphosphate, are suitable as water-soluble inorganic builder materials. In particular, the crystalline or amorphous alkali aluminosilicate can be present in an amount of up to 50 wt.%, Preferably of up to 40 wt.%, As a water-insoluble, water-dispersible inorganic builder material, To 5 wt.%. Among these, the cleaning agent grades of crystalline sodium aluminosilicates, in particular zeolites A, P and optionally X, are preferred. An amount close to the specified upper limit value is preferably used for the solid particulate agonist. Suitable aluminosilicates have in particular no particles with a particle size of more than 30 [mu] m, preferably at least 80 wt% of particles having a size of less than 10 [mu] m.

A suitable alternate or partial replacement for the stated aluminosilicate is a crystalline alkali silicate, which may be present alone or in admixture with an amorphous silicate. Alkali silicates which can be used as builders in the agents according to the invention preferably have a molar ratio of alkali oxides to SiO ₂ of less than 0.95, in particular from 1: 1.1 to 1:12, and may be present in amorphous or crystalline form. Preferred alkali silicates are sodium silicates, especially amorphous sodium silicates, having a Na ₂ O: SiO ₂ molar ratio of 1: 2 to 1: 2.8. Wherein the coefficient is a number from 1.9 to 4, y is a number from 0 to 20, and a preferred value for x is 2, 3 or 4, with the formula Na ₂ Si _x O _{2x + 1} .y H ₂ O ) Of crystalline silicate are preferably used as the crystalline silicate, which may be present alone or in admixture with an amorphous silicate. Preferred crystalline filo silicates are those in which x in the specified formula takes a value of 2 or 3. In particular, both beta-sodium and delta-sodium disilicate (Na ₂ Si ₂ O ₅ .y H ₂ O) are preferred. In fact, anhydrous crystalline alkali silicates having the above formula in which x is a number from 1.9 to 2.1 and made from amorphous alkali silicates can also be used in the agents according to the invention. In a further preferred embodiment of the agent according to the invention crystalline sodium phyllosilicates having a modulus of from 2 to 3 are used, which can be prepared from sand and soda. Crystalline sodium silicates with a modulus in the range of 1.9 to 3.5 are used in further preferred embodiments of the agents according to the invention. In the case where alkali aluminosilicates, especially zeolites, are also present as additional builders, the weight ratio of aluminosilicate to silicate is preferably 1:10 to 10: 1, based on the anhydrous active material in each case. In the agents containing both amorphous and crystalline alkali silicates, the weight ratio of amorphous alkaline silicate to crystalline alkali silicate is preferably from 1: 2 to 2: 1, especially from 1: 1 to 2: 1.

The builder, if desired, is contained in the agent according to the invention preferably in an amount of at most 60 wt.%, Especially 5 wt.% To 40 wt.%. The post-laundry treatment agents according to the invention, for example softeners, preferably do not contain an inorganic builder.

Suitable peroxygen compounds are, in particular, salts of perborates of organic peracids or organic acids such as salts of phthalimidopercarphonic acid, perbenzoic acid, or dipredocandioic acid, hydrogen peroxide, and inorganic salts which release hydrogen peroxide under the conditions of use, Percarbonates and / or persilicates. When solid and oxygen compounds are intended to be used, they can be used in powder or granular form, and they can also be coated in a theoretically known manner. With alkaline percarbonate, alkaline perborate monohydrate or especially liquid agents, the optional use of hydrogen peroxide in the form of an aqueous solution containing from 3 wt.% To 10 wt.% Of hydrogen peroxide is particularly preferred. If the agent according to the invention contains a bleaching agent, such as preferably an over oxygen compound, they are preferably present in an amount of at most 50 wt.%, In particular from 5 wt.% To 30 wt.%. Addition of minor amounts of known bleach stabilizers such as phosphonates, borates or metaborates, metasilicates and magnesium salts such as magnesium sulphate may be convenient.

And compounds which produce aliphatic peroxocarboxylic acids and / or optionally substituted perbenzoic acids, preferably having from 1 to 10 carbon atoms, especially from 2 to 4 carbon atoms, under hydrolysis conditions can be used as bleaching activators . Substances which have the specified number of C atoms of O acyl and / or N acyl groups and / or optionally substituted benzoyl groups are suitable. Polyacylated alkylenediamines, especially tetraacetylethylenediamine (TAED), acylated triazine derivatives, especially 1,5-diacetyl-2,4-dioxo-hexahydro-1,3,5-triazine DADHT), acylated glycolurils, especially tetraacetyl glycoluril (TAGU), N-acylimides, especially N-nonanoylsuccinimide (NOSI), acylated phenolsulfonates, especially n-nonanoyl - or isononanoyloxybenzenesulfonate (n- or iso-NOBS), carboxylic acid anhydrides, in particular phthalic anhydride, acylated polyhydric alcohols, in particular triacetin, ethylene glycol diacetate, 2,5-diacetoxy -2,5-dihydrofuran and enol esters, and acetylated sorbitol and mannitol or mixtures thereof (SORMAN), acylated sugar derivatives, in particular pentaacetyl glucose (PAG), pentaacetyl fructose, tetraacetyl xylulose and Octacetyllactose, and acetylated, optionally N-alkylated Glucamine and gluconolactone, and / or N-acylated lactam, such as N-benzoylcaprolactam, are preferred. Hydrolytically substituted acyl acetals and acyl lactams are likewise preferably used. Combinations of conventional bleach activators may also be used. Bleach activators of this kind may be contained in a typical amount range, preferably in an amount of from 1 wt.% To 10 wt.%, Especially from 2 wt.% To 8 wt.%, Based on the total agent .

In addition to or instead of the conventional bleach activators listed above, sulfonimine and / or bleach-enhancement transition metal salts or transition metal complexes may also be included as so-called bleach catalysts.

Suitable enzymes that can be used in the agonists are those of the protease, cutinase, amylase, pullulanase, hemicellulase, cellulase, lipase, oxidase and peroxidase classes, and mixtures thereof. Fungi or bacteria such as Bacillus subtilis , Bacillus licheniformis , Streptomyces griseus , Humicola lanuginosa , Humicola insolens , Pseudomonas pseudoalcaligenes or Pseudomonas cepacia are particularly suitable. Optionally used enzymes can be adsorbed on the carrier material and / or embedded in the coating material to protect the enzyme from premature inactivation. The enzyme, if desired, is contained in the agent according to the invention preferably in an amount of 5 wt.% Or less, especially 0.2 wt.% To 2 wt.%.

The agent may optionally contain, for example, a derivative of diaminostilbenyl disulfonic acid or an alkali metal salt thereof as optical brightener. For example, salts of 4,4'-bis (2-anilino-4-morpholino-1,3,5-triazinyl-6-amino) stilbene-2,2'- disulfonic acid, A compound having a similar structure having a diethanolamino group, a methylamino group, an anilino group or a 2-methoxyethylamino group instead of a polyno group is suitable.

Suitable zwitterionic agents include, for example, mixtures of organopolysiloxanes and their superfine particles, optionally silanized silicic acid, and paraffin waxes and mixtures thereof with silanized silicic acid or bis-fatty acid alkylenediamides. Mixtures of various foams, such as those composed of, for example, silicone, paraffin or wax, are also advantageously used. Zwitter agents, especially silicone and / or paraffin-containing zwitter agents, are preferably bound to a water-soluble or water-dispersible granular carrier material. Mixtures of paraffin wax and nonstearyl ethylenediamides are particularly preferred.

In addition, the agonist may also contain components that positively affect the ability to wash away oil and grease from the textile, or so-called pollution-free active ingredients. This effect is particularly evident when the textile, which has previously been washed several times with the functional agent according to the invention containing such oils and grease-soluble components, is contaminated. Preferred oil and grease-dissolving components are, for example, 15 to 30 wt.% Of methoxyl groups and 1 to 15 wt.% Of nonionic cellulose ethers such as methylcellulose and, in each case, nonionic cellulose ethers. Methylhydroxypropylcellulose having a proportion of hydroxypropoxyl groups in the% by weight and polymers of phthalic acid and / or terephthalic acid known from the prior art, or derivatives thereof with monomeric and / or polymeric diols, in particular ethylene terephthalate and / / Or a polymer of polyethylene glycol terephthalate or an anionic and / or non-ionically modified derivative thereof.

The agent may also contain a dye inhibitor, preferably in an amount of 0.1 wt.% To 2 wt.%, Especially 0.1 wt.% To 1 wt.%, Which, in a preferred embodiment of the invention, Vinyl imidazole or a polymer of vinyl pyridine-N-oxide or a copolymer thereof.

The function of the graying inhibitor is to keep the contaminants removed from the textile fibers in suspension in the liquid. Salts of organic, water soluble colloids, such as starch, sizing agents, gelatin, starch or a salt of an ether carboxylic acid or ether sulphonic acid, or an acidic sulfuric acid ester of cellulose or starch, are suitable for this purpose. Water-soluble polyamides containing acidic groups are also suitable for this purpose. Starch derivatives other than those mentioned above, such as aldehyde starches, may also be used. Cellulose ethers such as carboxymethylcellulose (Na salt), methylcellulose, hydroxyalkylcellulose, and mixed ethers such as methylhydroxyethylcellulose, methylhydroxypropylcellulose, methylcarboxymethylcellulose, and mixtures thereof, For example, it may be used in an amount of 0.1 to 5 wt.%, Based on the agent.

The organic solvents which can be used in the agents according to the invention are in particular alcohols having from 1 to 4 carbon atoms, especially methanol, ethanol, isopropanol, and tert-butanol, in particular in the presence of the agent in liquid or paste- Diols having 2 to 4 carbon atoms, especially ethylene glycol and propylene glycol, and mixtures thereof, and ethers derived from the class of compounds mentioned. This type of water-miscible solvent is preferably present in the agent according to the invention in an amount of up to 30 wt.%, In particular from 6 wt.% To 20 wt.%.

To set the desired pH that is not naturally caused by mixing other components, the agents according to the invention may be used in combination with acids which are compatible with the system and the environment, especially citric acid, acetic acid, tartaric acid, malic acid, lactic acid, glycolic acid, Glutaric acid, and / or adipic acid as well as inorganic acids, especially sulfuric acid, or bases, especially ammonium or alkaline hydroxides. This type of pH controlling agent is optionally contained in the agent according to the invention, preferably in an amount of up to 20 wt.%, In particular from 1.2 wt.% To 17 wt.%.

The preparation of the solid agonists according to the invention (i. E. In particular washing or cleaning agents) does not present any difficulties and can be achieved in the theoretically known manner, for example by spray drying or granulation, The compound and optional bleach catalyst are optionally added separately in subsequent stages. For the preparation of the agents according to the invention having an increased bulk weight, in particular a bulk weight in the range from 650 g / l to 950 g / l, a process with an extrusion step is preferred. The preparation of the liquid agent according to the invention also does not present any difficulties and can be achieved in a similar manner as well.

The preparation of compounds of formula (I) according to the present invention is described in the Examples section with reference to the preparation of precursor-aromatics containing undecan-2-one as an example. Other compounds of formulas (I), (II), (III) and (IV) may also be prepared via these basic synthetic routes.

According to a preferred embodiment, the teaching according to the invention can be used to significantly reduce the percentage of perfume in the cleaning, cleaning and body management agents. Thus, it is also possible, due to the specific intolerance and stimulation, to provide a particularly delicate consumer with a perfume additive product which can only be used on a limited basis, or not at all, with conventional parfum added products.

In various embodiments of the present invention, the cleaning or cleaning agent is present in liquid or solid form.

The preferred solids, in particular the powdered cleansing agents according to the invention, in addition to the compounds according to the invention may also contain in particular, for example, constituents selected from the following:

Preferably an anionic surfactant in an amount of, for example, from 5 to 30 wt.%, For example an alkylbenzenesulfonate, an alkyl sulfate,

- nonionic surfactants in an amount of, for example, preferably from 0.5 to 15 wt.%, Such as fatty alcohol polyglycol ethers, alkylpolyglucosides, fatty acid glucamides,

Builders in the amount of from 0 to 70 wt.%, Advantageously from 5 to 60 wt.%, Preferably from 10 to 55 wt.%, Especially from 15 to 40 wt.%, For example zeolites, Decylate, sodium citrate,

For example from 0 to 35 wt.%, Advantageously from 1 to 30 wt.%, Preferably from 2 to 25 wt.%, Especially from 5 to 20 wt.%, Of an alkali such as sodium carbonate,

For example from 0 to 30 wt.%, Advantageously from 5 to 25 wt.%, Preferably from 10 to 20 wt.%, Of a bleaching agent such as sodium perborate, sodium percarbonate,

For example from 0 to 10 wt.%, Advantageously from 1 to 6 wt.%, Preferably from 2 to 5 wt.%, Especially from 3 to 4 wt.%, Of corrosion inhibitors such as sodium silicate,

Advantageously from 0 to 1 wt.% Of a stabilizer, for example a phosphonate,

Advantageously from 0 to 4 wt.%, Preferably from 0.1 to 3 wt.%, Especially from 0.2 to 1 wt.%, Of a wadding agent such as soap, silicone oil, paraffin,

Advantageously 0 to 2 wt.%, Preferably 0.2 to 1 wt.%, Especially 0.3 to 0.8 wt.% Of enzymes such as proteases, amylases, cellulases,

- advantageously 0 to 1 wt.% Of a graying inhibitor, for example carboxymethylcellulose,

- preferably 0 to 2 wt.% Of a discoloration inhibitor such as a polyvinyl pyrrolidone derivative,

- advantageously from 0 to 20 wt.% Of a modifier, for example sodium sulphate,

Advantageously from 0 to 0.4 wt.%, In particular from 0.1 to 0.3 wt.%, Of an optical brightener, for example a stilbene derivative, a biphenyl derivative,

- optionally additional fragrances,

- optionally water,

- optionally soap,

Optionally bleach activator,

Optionally cellulose derivatives,

- optionally an antifouling agent,

In each case wt.% Is given on a total agonist basis.

In another preferred embodiment of the present invention, the agent is present in a liquid form, preferably in the form of a gel. Preferred liquid washing or cleaning agents and cosmetics have a water content of, for example, 10 to 95 wt.%, Preferably 20 to 80 wt.%, In particular 30 to 70 wt.%, Based on the total agent. In the case of liquid concentrates, the water content can also be particularly low, for example <30 wt.%, Preferably <20 wt.%, Especially <15 wt.% And in each case wt. It is based on agonists. Liquid agonists may also contain non-aqueous solvents.

Preferred liquids according to the invention, in particular gel-washing agents, may additionally contain, in addition to the compounds according to the invention, in particular, for example,

Preferably an anionic surfactant in an amount of, for example, from 5 to 40 wt.%, For example an alkylbenzenesulfonate, an alkyl sulphate,

- nonionic surfactants in an amount of, for example, preferably from 0.5 to 25 wt.%, Such as preferably fatty alcohol polyglycol ethers, alkylpolyglucosides, fatty acid glucamides,

Advantageously from 0 to 15 wt.%, Preferably from 0.01 to 10 wt.%, In particular from 0.1 to 5 wt.% Builder, such as zeolite, polycarboxylate, sodium citrate,

For example from 0 to 10 wt.%, Advantageously from 0.1 to 4 wt.%, Preferably from 0.2 to 2 wt.%, Especially from 1 to 3 wt.%, Oil, paraffin,

For example from 0 to 3 wt.%, Advantageously from 0.1 to 2 wt.%, Preferably from 0.2 to 1 wt.%, Especially from 0.3 to 0.8 wt.%, Of enzymes such as proteases, amylases, Cellulase, lipase,

For example from 0 to 1 wt.%, Advantageously from 0.1 to 0.3 wt.%, In particular from 0.1 to 0.4 wt.%, Of an optical brightener, for example a stilbene derivative, a biphenyl derivative,

- optionally additional fragrances,

Optionally stabilizing agent,

- water

- optionally an amount of soap, for example from 0 to 25 wt.%, Advantageously from 1 to 20 wt.%, Preferably from 2 to 15 wt.%, Especially from 5 to 10 wt.%,

Optionally, advantageously from 0 to 25 wt.%, Preferably from 1 to 20 wt.%, In particular from 2 to 15 wt.%, Of a solvent (preferably an alcohol)

In each case wt.% Is given on a total agonist basis.

The preferred liquid softening agents according to the invention may additionally comprise, in addition to the ketones according to the invention, especially the following selected components:

- cationic surfactants in an amount of, for example, from 5 to 30 wt.%, Such as in particular ester quats,

- co-surfactants in amounts of, for example, from 0 to 5 wt.%, Preferably from 0.1 to 4 wt.%, Such as glycerol monostearate, stearic acid, fatty alcohols, fatty alcohol ethoxylates,

An emulsifier in an amount of, for example, 0 to 4 wt.%, Preferably 0.1 to 3 wt.%, For example a fatty amine ethoxylate,

- optionally additional fragrances,

Preferably in the ppm range of the dye,

A stabilizing agent, preferably in the ppm range,

Preferably in an amount of 60 to 90 wt.%, Such as water,

In each case wt.% Is given on a total agonist basis.

A further object of the present invention relates to a method for long term sustained smell of a surface comprising the steps of applying a compound according to the invention of formula (I) or a cleaning or cleaning agent according to the invention, a cosmetic agent or an air- Such as textiles, dishes, floors, and then exposing the surface to conditions that provide for hydrolysis of the bulb-fragrance.

Example

Example 1: Synthesis of undecanone based on L - (-) - sorbose

Stage 1: 2,2-dimethoxyundecane

Toluene-4-sulfonic acid (1.90 g, 10 mmol) was heated repeatedly in a 500 ml Schlenk flask under vacuum (approximately 0.1 mbar) and argon was added thereto repeatedly. Methanol (80 ml) and 2,2-dimethoxypropane (208.3 g, 2.0 mol) were then added via a septum stopper. The reaction mixture was then cooled to approximately -50 C and undecan-2-one (17.0 g, 100 mmol) was added dropwise. The mixture was stirred at -50 &lt; 0 &gt; C for 4 hours, then cooling was stopped and the mixture was heated to room temperature overnight. After heating to 50 &lt; 0 &gt; C, the reaction mixture was stirred at this temperature for a further 7 hours. The mixture cooled to room temperature was washed twice with cold saturated NaHCO ₃ solution, washed once with saturated NaCl solution, dried over MgSO ₄ , filtered, and concentrated under reduced pressure, , And concentrated on a rotary evaporator. 18.1 g (yield: 13.5 g, 62.6 mmol, 63%) of a yellow, clear oil were obtained (2,2-dimethoxyundecane: undecanone; 7: 3).

Stage 2: Undecanone based on L - (-) - sorbose

(2.61 g, 12.1 mmol) was dissolved in 10 ml of THF with a mixture of undecanone (2.88 g, 16.9 mmol) and L- (-) - sorbose (1.14 g, 6.34 mmol ) And zinc (II) chloride (11.0 mg, 59.0 μmol) were added under reflux of argon, and the mixture was stirred at 70 ° C. for 41 hours. The cooled suspension to room temperature was filtered through a frit after the addition of triethylamine (30 [mu] l) and stirring for a short period, then the filtrate was concentrated under reduced pressure. After purification by column chromatography (pentane: ethyl acetate gradient 95: 5 to 70:30, containing 1% triethylamine), two product fractions were obtained (isomer 1: 210 mg, 433 μmol, isomer 2: 430 mg, 888 [mu] mol, 21% yield).

Example 2: Release behavior

The test substance was dissolved in an equimolar amount of diethyl ether as compared to the fragrance contained therein, and then pipetted onto the fragrance strip. The strips treated in this manner were then stored at room temperature and the strength of the fragrance was graded to a scale of 1 to 10 (10 = intense odor, 0 = no odor) assessed by odor. To evaluate the boost effect, test strips were sprayed at various time points with an aqueous pH buffer system and subsequently similarly assessed by smell. The isomer 1 obtained in Stage 2 of Example 1 was the object of the test.

Claims (12)

The compound of formula (I)

here
Ra and Rb together with the C atom to which they are attached form a linear, branched, saturated or unsaturated, branched or cyclic hydrocarbon radical having from 6 to 30, preferably from 6 to 20 carbon atoms and from 0 to 10 heteroatoms selected from N, O, S and Si Or a cyclic, substituted or unsubstituted hydrocarbon functional group or, together with the C atom to which they are attached, form a cyclic hydrocarbon functional group and is derived from a directional ketone of the formula Ra-C (O) -Rb; Each of R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ is independently selected from the group consisting of hydrogen, -OR x, -NR x R y, halogen, a substituent having up to 20, Linear or branched alkyl, alkenyl or alkynyl, up to 20, preferably up to 12 carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, Substituted or unsubstituted, linear or branched heteroalkyl, heteroalkenyl or heteroalkynyl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 20, Substituted or unsubstituted heteroaryl having up to 12 carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, up to 20, preferably up to 12 carbon atoms Lt; RTI ID = 0.0 &gt; cycloalkyl &lt; / RTI & , And heterocycloalkyl or heterocycloalkenyl having up to 20, preferably up to 12, carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N from the group consisting of Or two of R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ in each case are substituted or unsubstituted aryl having up to 20, preferably up to 12 carbon atoms, Substituted or unsubstituted heteroaryl having up to 20, preferably up to 12, carbon atoms and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, up to 20, Substituted or unsubstituted cycloalkyl or cycloalkenyl having up to 12 carbon atoms and up to 20, preferably up to 12 carbon atoms and 1 to 6, preferably 1 &lt; RTI ID = 0.0 &gt; Four to four As may be combined with each other to form click group when selected from substituted or unsubstituted heterocycloalkyl or heteroaryl cycloalkenyl unsubstituted alkenyl having atoms, where _{R 1, R 2, R 3} , R 4, R 5 and R ₆ Is at least one functional group of the formula -ORx or contains a functional group of the above formula as a substituent; Rx and Ry are substituted or unsubstituted, linear or branched alkyl, alkenyl or alkynyl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms And substituted or unsubstituted, linear or branched, heteroalkyl, heteroalkenyl or heteroalkynyl having 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, up to 20, Substituted or unsubstituted aryl having up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms, and 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, Cycloalkyl or cycloalkenyl having up to 20, preferably up to 12 carbon atoms, and up to 20, preferably up to 12 carbon atoms and O, S and N U From 1 to 6 selected, and preferably is selected from heterocycloalkyl or heteroaryl, cycloalkenyl having from 1 to 4 heteroatoms; n is 0, 1, 2 or 3; 2. A compound according to claim ₁ , wherein R ₁ , R ₂ and R ₄ are hydrogen and R ₃ is preferably selected from the group consisting of 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms, Lt; / RTI &gt; is a substituted alkyl or heteroalkyl functionality having one or more substituents. 3. A compound according to claim 1 or 2, characterized in that the compound is a compound of formula (II)

Wherein R a, R b, R ₁ , R ₂ , R ₄ , R ₅ , R ₆ and n are as defined in claim 1 or 2;
_{Ra ', Rb', R 1} ', R 2', R 4 ', R 5' and R ₆ 'are the Ra, Rb, R ₁ in one of the preceding _{claims, R 2, R 4, R} 5 And R &lt; ₆ &gt; and are independently selected;
Rc and Rd are independently selected from the group consisting of hydrogen, -ORx, -NRxRy, halogen, substituted or unsubstituted, linear or branched alkyl, alkenyl, or alkynyl having up to 20, preferably up to 12 carbon atoms, Substituted or unsubstituted, linear or branched, heteroalkyl having 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, Substituted or unsubstituted aryl having up to 20, preferably up to 12 carbon atoms, up to 20, preferably up to 12 carbon atoms and 1 to 6 selected from O, S and N, Preferably a substituted or unsubstituted heteroaryl having 1 to 4 heteroatoms, cycloalkyl or cycloalkenyl having up to 20, preferably up to 12 carbon atoms, and up to 20, preferably up to 20, Heterocycloalkyl or heterocycloalkenyl having 1 to 6, preferably 1 to 4, heteroatoms selected from O, S and N, or one of Rc and Rd is selected from the group consisting of R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₁ ', R ₂ ', R ₃ ', R ₄ ', and R ₅ ' And R &lt; ₆ &gt;';
Rx and Ry are as defined in claim 1;
m is 0 or an integer from 1 to 10, preferably 0, 1, 2 or 3, particularly preferably 1 or 2, most preferably 2. 4. A compound according to claim 3, characterized by:
(1) R ₁ , R ₂ , R ₄ , R ₁ ', R ₂ ' and R ₄ 'are hydrogen; And / or
(2) n is 0 or 1, particularly preferably 0 in all cases. 5. A compound according to any one of claims 1 to 4, characterized in that the compound is a compound of formula (III) or (IV)

Wherein Ra, Rb, Ra 'and Rb' are as defined in any one of claims 1 to 4 and are in particular of the formula Ra-C (O) -Rb or Ra'-C (O) It is a functional group derived from an aromatic ketone. 6. The compound according to any one of claims 1 to 5, wherein Ra and Rb and the C atom to which they are bonded and / or Ra ', Rb' and the C atom to which they are bonded are a functional group derived from an aromatic ketone, Silver bicomponent; Isozyme; Methyl beta-naphthyl ketone; Musk indanone; Tonal Lead / Musk Plus; Alpha - Damascus; Beta - Damascus; Delta - Damascon; Gamma-damascone; Damascenone; Damask Rose; Methyl dihydroazosumonate (hedione); Mentone; Carbon; Camphor; Penchon; Alpha-ionone; Beta-ionone; Gamma-methylionone; Flouramon; Dihydrozase; Cis-jasmone; Iso E super (1- (1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthyl) ethan-1-one); Methyl sedrenyl ketone; Methyl cephalorone; Acetophenone; Methyl acetophenone; Para-methoxyacetophenone; Methyl beta-naphthyl ketone; Benzyl acetone; Benzophenone; Para-hydroxyphenylbutanone; Celery ketone or ribcone; 6-isopropyldecahydro-2-naphthone; Dimethyloctenone; Presscommente; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; Methylheptenone; 2- (2- (4-methyl-3-cyclohexen-1-yl) propyl) cyclopentanone; 1- (p-menthene-6 (2) yl) -1-propanone; 4- (4-hydroxy-3-methoxyphenyl) -2-butanone; 2-acetyl-3, 3-dimethylnorbornane; 6,7-dihydro-1,1,2,3,3-pentamethyl-4 (5H) indanone; 4-damascone (5-methyl-5-phenyl-3-hexanone); Dulsinium; Carcion; Gelson; Hexalone; Isocyclemone E; Methylcyclotetrone; Methyl lavender ketone; Duck bone; Para-tert-butylcyclohexanone; Verdon; Delphon; Muscons; Neobutenone; Flicaton; Bellows; 2,4,4,7-tetramethyl-oct-6-en-3-one; Tetramerane; 4-methoxyphenyl-ethanone; 1- [6- (1,1-Dimethylethyl) -2,3-dihydro-1,1-dimethyl-1H-inden-4-yl] ethanone; 1- (5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl) ethanone; 2- (1-methylethyl) -indanone; 4-tert-butyl-3,5-dinitro-2,6-dimethyl-acetophenone; 1,6,7,8-tetrahydro-1,4,6,6,8,8-hexamethyl-as-indacene-3 (2H) -one; 1- (2-Daphthalenyl) ethanone; 1- (2,3-dihydro-1,1,2,3,3,6-hexamethyl-1H-inden-5-yl) ethanone; 1- [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1H-inden-5-yl] ethanone; 3-methyl-1- (4-methylphenyl) -4-hexen-1-one; 5-acetyl-1,1,2,3,3-pentamethylindane; 1-phenylpropanone; Acetophenone; 2,4-dimethylphenyl-ethanone; 1- [4- (1,1-dimethylethyl) -2,6-dimethylphenyl] ethanone; 1- (hexahydrodimethyl-1H-benzindenyl) ethanone; 1- (5,6,7,8-tetrahydro-2-naphthalenyl) ethanone; 1-phenyl-4-penten-1-one; 1- (5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl) ethanone; 1- (3-ethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl) ethanone; 2,5-dimethyl-oct-2-en-6-one; 4- (2,6,6-trimethylcyclohex-1-en-1-yl) -butan-2-one; 4- (2,6,6-trimethylcyclohex-2-en-1-yl) -butan-2-one; 2-methyl-5- (1-methylethenyl) -cyclohex-2-en-1-one; 1- (4-hydroxyphenyl) -butan-3-one; 4-Benzo-1, 3-dioxo-5-yl-but-2-one; 2-heptyl-cyclopentanon-nonan-2-one; Oct-2-one; 2,2,6,10-tetramethyltricyclo- [5.4.0.0 (6,10)] undecan-4-one; Heptan-2-one; Undecan-2-one; Decan-2-one; Benzyl acetone; Butan-2-one; 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one; 6-methyl-hept-5-en-2-one; 2- (butan-2-yl) -cyclohexanone; 2-hexyl-cyclopent-2-en-1-one; 2- (1-methylethyl) -5-methyl-cyclohexanone; 2- (2-methylethyl) -5-methyl-cyclohexanone; 3-methyl-cyclopentadecanone; 4- (1,1-dimethylpropyl) -cyclohexanone; 6,10-dimethyl-undeca-5,9-dien-2-one; 3-oxo-2-pentyl-cyclopentane-acetic acid-methyl ester; 1- (1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl) ethanone; 3-methyl-5-propyl-cyclohex-2-en-1-one; 1- (2-cyclohexene) -2,4,4-trimethyl-but-2-enone; Carbon; 2-hexyl-cyclo-pent-2-en-1-one; 2-pentyl-cyclopent-2-en-1-one; 3-methyl-2-pentyl-cyclopent-2-en-1-one; 2-hexylidene-cyclopentanone; 3,5-diethyl-5,6-dimethyl-2-cyclohexenone; 4,4a, 5,6,7,8-hexahydro-6-isopropenyl-4,4a-dimethyl-2 (3H) -naphthalenone; 3-methyl-6-propylidene cyclohexanone; 4- (1-methylethyl) -cyclohex-2-en-1-one; (E) -oct-3-en-2-one; 1- (2,3,4,7,8,8A-hexahydro-3,6,8,8-tetramethyl-1H-3a, 7-methanoazulen-5-yl) -ethanone; 2-hydroxy-3,5-dimethyl-cyclopent-2-en-1-one; 1- (3,3-dimethyl-1-cyclohexen-1-yl) ethanone; 1- (2,4,6-trimethylcyclohex-3-en-1-yl) -but-1-en-3-one; Acetylisothiophenol; 2- (3-methylbut-2-en-1-yl) -3-methyl-cyclopent-2-en-1-one; 3-methyl-5- (2,2,3-trimethylcyclopent-3-en-1-yl) pent-3-en-2-one; 5-butylidene-2,2,4-trimethylcyclopentanone; 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one; 3-methyl-5-propyl-cyclohex-2-en-1-one; 4,4a, 5,6,7,8-hexahydro-6-isopropyl-2 (3H) -naphthalinone; 3,5,5-trimethyl-cyclohex-2-ene-1,4-dione; (E) -5-methyl-2-hepten-4-one; Acetyl diisoamylen; Des-3-en-2-one; 2-ethyl-3,6,6-trimethylcyclohex-2-enyl-but-2-en-1-one; 1- (5,5-dimethyl-1 (6) -cyclohexen-1-yl) -4-penten-1-one; 1- (2,6,6-trimethyl-1-cyclohexen-1-yl) but-2-en-1-one; 1- (2,6,6-trimethyl-2-cyclohexen-1-yl) but-2-en-1-one; 1- (2,6,6-trimethyl-3-cyclohexen-1-yl) but-2-en-1-one; 2,4,4,5,5-pentamethyl-1-cyclopenten-1-yl-ethanone. A cleaning or cleaning agent comprising at least one compound according to any one of claims 1 to 6. 8. A cleaning or cleaning agent according to claim 7, characterized by:
a. At least one compound is present in an amount of 0.0001 to 5 wt.%, Preferably 0.001 to 4 wt.%, More preferably 0.005 to 3 wt.%, Particularly preferably 0.001 to 5 wt.%, 0.01 to 2 wt.%, And / or
b. Wherein the cleaning or cleaning agent comprises at least one surfactant selected from the group consisting of anionic, cationic, nonionic, zwitterionic, amphoteric surfactants and mixtures thereof, and / or
c. Cleaning or cleaning agent present in liquid or solid form. 7. Air-management agent comprising at least one compound according to any one of claims 1 to 6, characterized in that the specified compound is in each case 0.0001 to 50 wt.%, Is contained in an amount of 0.001 to 5 wt.%, More preferably 0.01 to 3 wt.%, Particularly preferably 0.1 to 2 wt.%. An insect repellent agent comprising at least one compound according to any one of claims 1 to 6, characterized in that the specified compound is in each case 0.0001 to 100 wt.%, Is contained in an amount of 0.001 to 50 wt.%, More preferably 0.1 to 30 wt.%, Particularly preferably 1 to 20 wt.%. 7. A cosmetic agent comprising at least one compound according to any one of claims 1 to 6, characterized in that the specified compound is present in each case in an amount of from 0.0001 to 50 wt.%, Is contained in an amount of 0.001 to 5 wt.%, More preferably 0.005 to 3 wt.%, Particularly preferably 0.01 to 2 wt.%. A method for the long-term sustained smell of the surface and / or the elimination of insects, comprising applying a compound according to any one of claims 1 to 6 to a surface to be smudged, Lt; RTI ID = 0.0 &gt; condition. &Lt; / RTI &gt;